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Article

Eco-Friendly 1,3-Dipolar Cycloaddition Reactions on Graphene Quantum Dots in Natural Deep Eutectic Solvent

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Department of Chemical, Biological, Pharmaceutical and Environmental Sciences, University of Messina, I-98168 Messina, Italy
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Department of Chemistry, Biology and Biotechnology, University of Perugia, I-06123 Perugia, Italy
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Department of Engineering, University of Messina, I-98166 Messina, Italy
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Department of Mathematical and Computer Sciences, Physical Sciences and Earth Sciences, University of Messina, I-98166 Messina, Italy
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Department of Civil, Energy, Environmental and Materials Engineering, Mediterranea University, I-89122 Reggio Calabria, Italy
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Department of Chemical Sciences, University of Catania and I.N.S.T.M. UdR of Catania, I-95125 Catania, Italy
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Institute for Microelectronics and Microsystems, National Research Council (CNR-IMM), Ottava Strada n.5, I-95121 Catania, Italy
*
Author to whom correspondence should be addressed.
Nanomaterials 2020, 10(12), 2549; https://doi.org/10.3390/nano10122549
Received: 24 November 2020 / Revised: 15 December 2020 / Accepted: 16 December 2020 / Published: 18 December 2020
Due to their outstanding physicochemical properties, the next generation of the graphene family—graphene quantum dots (GQDs)—are at the cutting edge of nanotechnology development. GQDs generally possess many hydrophilic functionalities which allow their dispersibility in water but, on the other hand, could interfere with reactions that are mainly performed in organic solvents, as for cycloaddition reactions. We investigated the 1,3-dipolar cycloaddition (1,3-DCA) reactions of the C-ethoxycarbonyl N-methyl nitrone 1a and the newly synthesized C-diethoxyphosphorylpropilidene N-benzyl nitrone 1b with the surface of GQDs, affording the isoxazolidine cycloadducts isox-GQDs 2a and isox-GQDs 2b. Reactions were performed in mild and eco-friendly conditions, through the use of a natural deep eutectic solvent (NADES), free of chloride or any metal ions in its composition, and formed by the zwitterionic trimethylglycine as the -bond acceptor, and glycolic acid as the hydrogen-bond donor. The results reported in this study have for the first time proved the possibility of performing cycloaddition reactions directly to the p-cloud of the GQDs surface. The use of DES for the cycloaddition reactions on GQDs, other than to improve the solubility of reactants, has been shown to bring additional advantages because of the great affinity of these green solvents with aromatic systems. View Full-Text
Keywords: graphene quantum dots; 1,3-dipolar cycloadditions; natural deep eutectic solvents; eco-friendly reactions graphene quantum dots; 1,3-dipolar cycloadditions; natural deep eutectic solvents; eco-friendly reactions
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MDPI and ACS Style

Giofrè, S.V.; Tiecco, M.; Celesti, C.; Patanè, S.; Triolo, C.; Gulino, A.; Spitaleri, L.; Scalese, S.; Scuderi, M.; Iannazzo, D. Eco-Friendly 1,3-Dipolar Cycloaddition Reactions on Graphene Quantum Dots in Natural Deep Eutectic Solvent. Nanomaterials 2020, 10, 2549. https://doi.org/10.3390/nano10122549

AMA Style

Giofrè SV, Tiecco M, Celesti C, Patanè S, Triolo C, Gulino A, Spitaleri L, Scalese S, Scuderi M, Iannazzo D. Eco-Friendly 1,3-Dipolar Cycloaddition Reactions on Graphene Quantum Dots in Natural Deep Eutectic Solvent. Nanomaterials. 2020; 10(12):2549. https://doi.org/10.3390/nano10122549

Chicago/Turabian Style

Giofrè, Salvatore V., Matteo Tiecco, Consuelo Celesti, Salvatore Patanè, Claudia Triolo, Antonino Gulino, Luca Spitaleri, Silvia Scalese, Mario Scuderi, and Daniela Iannazzo. 2020. "Eco-Friendly 1,3-Dipolar Cycloaddition Reactions on Graphene Quantum Dots in Natural Deep Eutectic Solvent" Nanomaterials 10, no. 12: 2549. https://doi.org/10.3390/nano10122549

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